메뉴 건너뛰기




Volumn 6, Issue 6, 2009, Pages 445-450

Synthesis and pharmacological activity of thiourea derivatives of 1,7,8,9-tetramethyl-4-azatricyclo [5.2.1.02,6]dec-8-ene-3,5-dione

Author keywords

Pharmacological activity; Thiourea derivatives; X ray analysis

Indexed keywords

1 (1 PHENYL ETHYL) 3 (1,7,8,9 TETRAMETHYL 3,5 DIOXO 4 AZATRICYCLO[5.2.1.0 2,6]DEC 8 EN 4 YL)THIOUREA; 1 (2 PHENYL ETHYL) 3 (1,7,8,9 TETRAMETHYL 3,5 DIOXO 4 AZATRICYCLO[5.2.1.0 2,6]DEC 8 EN 4 YL)THIOUREA; 1 (3,4 DICHLOROPHENYL) 3 (1,7,8,9 TETRAMETHYL 3,5 DIOXO 4 AZATRICYCLO[5.2.1.0 2,6]DEC 8 EN 4 YL)THIOUREA; 1 (4 CHLOROPHENYL) 3 (1,7,8,9 TETRAMETHYL 3,5 DIOXO 4 AZATRICYCLO[5.2.1.0 ,6]DEC 8 EN 4 YL)THIOUREA; 1 (4 IODOPHENYL) 3 (1,7,8,9 TETRAMETHYL 3,5 DIOXO 4 AZATRICYCLO[5.2.1.0 2,6]DEC 8 EN 4 YL)THIOUREA; 1 (4 METHOXYPHENYL) 3 (1,7,8,9 TETRAMETHYL 3,5 DIOXO 4 AZATRICYCLO[5.2.1.0 ,6]DEC 8 EN 4 YL)THIOUREA; 1 (ALLYL) 3 (1,7,8,9 TETRAMETHYL 3,5 DIOXO 4 AZATRICYCLO[5.2.1.0 2,6]DEC 8 EN 4 YL)THIOUREA; 1 (BENZOYL) 3 (1,7,8,9 TETRAMETHYL 3,5 DIOXO 4 AZATRICYCLO[5.2.1.0 2,6]DEC 8 EN 4 YL)THIOUREA; 1 (PHENYL) 3 (1,7,8,9 TETRAMETHYL 3,5 DIOXO 4 AZATRICYCLO[5.2.1.0 2,6]DEC 8 EN 4 YL)THIOUREA; 1 (PHENYLMETHYL) 3 (1,7,8,9 TETRAMETHYL 3,5 DIOXO 4 AZATRICYCLO[5.2.1.0 2,6]DEC 8 EN 4 YL)THIOUREA; 1,7,8,9 TETRAMETHYL 4 AZATRICYCLO[5.2.1.0 2,6]DEC 8 ENE 3,5 DIONE; 5 HYDROXYTRYPTOPHAN; SEROTONIN RECEPTOR; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

EID: 69549120492     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/157018009789057517     Document Type: Article
Times cited : (11)

References (44)
  • 1
    • 3042836102 scopus 로고    scopus 로고
    • Effect of stereochemistry on the anti-HIV activity of chiral thiourea compounds
    • Venkatachalam, T.K; Mao, C.; Uckun, F.M. Effect of stereochemistry on the anti-HIV activity of chiral thiourea compounds. Bioorg. Med. Chem., 2004, 12, 4275-4284.
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 4275-4284
    • Venkatachalam, T.K.1    Mao, C.2    Uckun, F.M.3
  • 6
    • 0029016056 scopus 로고
    • (+)-cis-4,5,7a,8,9,10,11,11a-octahydro-7H-10-methylindolo [1,7- Bc][2,6]-naphthyridine: A 5-HT2C/2B receptor antagonist with low 5-HT2A receptor affinity
    • Nozulak, J.; Kalkman, H.O.; Floerscheim, P.; Hoyer, D.; Schoeffer, P.; Buerki, H.R. (+)-cis-4,5,7a,8,9,10,11,11a-octahydro-7H-10-methylindolo [1,7- bc][2,6]-naphthyridine: a 5-HT2C/2B receptor antagonist with low 5-HT2A receptor affinity. J. Med. Chem., 1995, 38, 28-33.
    • (1995) J. Med. Chem. , vol.38 , pp. 28-33
    • Nozulak, J.1    Kalkman, H.O.2    Floerscheim, P.3    Hoyer, D.4    Schoeffer, P.5    Buerki, H.R.6
  • 7
    • 0029646696 scopus 로고
    • N-(1-methyl-5-indolyl)-N'-(3-methyl-5-isothiazolyl)urea: A novel, high-affinity 5-HT2B receptor antagonist
    • Forbes, I.T.; Jones, G.E.; Murphy, O.E.; Holland, V.; Baxter, G.S. N-(1-methyl-5-indolyl)-N'-(3-methyl-5-isothiazolyl)urea: a novel, high-affinity 5-HT2B receptor antagonist. J. Med. Chem., 1995, 38, 855-857.
    • (1995) J. Med. Chem. , vol.38 , pp. 855-857
    • Forbes, I.T.1    Jones, G.E.2    Murphy, O.E.3    Holland, V.4    Baxter, G.S.5
  • 8
    • 0023013871 scopus 로고
    • 2,3-Dialkyl(dimethylamino) indoles: Interaction with 5HT1, 5HT2, and rat stomach fundal serotonin receptors
    • Fludzinski, P.; Wittenauer, L.A.; Schenck, K.W.; Cohen, M.L. 2,3-Dialkyl(dimethylamino) indoles: interaction with 5HT1, 5HT2, and rat stomach fundal serotonin receptors. J. Med. Chem., 1986, 29, 2415-2418.
    • (1986) J. Med. Chem. , vol.29 , pp. 2415-2418
    • Fludzinski, P.1    Wittenauer, L.A.2    Schenck, K.W.3    Cohen, M.L.4
  • 10
    • 84883846031 scopus 로고
    • A method for assessing the effects of drugs on the central actions of 5-hydroxytryptamine
    • Corne, S.J.; Pickering, R.W.; Warner, B.T. A method for assessing the effects of drugs on the central actions of 5-hydroxytryptamine. Br. J. Pharmacol., 1963, 20,106-120.
    • (1963) Br. J. Pharmacol. , vol.20 , pp. 106-120
    • Corne, S.J.1    Pickering, R.W.2    Warner, B.T.3
  • 11
    • 0014165411 scopus 로고
    • A possible correlation between drug-induced hallucinations in man and a behavioural response in mice
    • Corne, S.J.; Pickering, R.W. A possible correlation between drug-induced hallucinations in man and a behavioural response in mice. Psychopharmacology, 1967, 11, 65-68.
    • (1967) Psychopharmacology , vol.11 , pp. 65-68
    • Corne, S.J.1    Pickering, R.W.2
  • 12
    • 0019793815 scopus 로고
    • Two distinct central serotonin receptors with different physiological functions
    • Peroutka, S.J.; Lebovitz, R.M.; Snyder, S.H. Two distinct central serotonin receptors with different physiological functions. Science, 1981, 212, 827-829. (Pubitemid 11069388)
    • (1981) Science , vol.212 , Issue.4496 , pp. 827-829
    • Peroutka, S.J.1    Lebovitz, R.M.2    Snyder, S.H.3
  • 13
    • 0020518358 scopus 로고
    • The head-twitch response to intraperitoneal injection of 5-hydroxytryptophan in the rat: Antagonist effects of purported 5-hydroxytryptamine antagonists and of pirenperone, an LSD antagonist
    • Colpaert, F.C.; Janssen, P.A. The head-twitch response to intraperitoneal injection of 5-hydroxytryptophan in the rat: antagonist effects of purported 5-hydroxytryptamine antagonists and of pirenperone, an LSD antagonist. Neuropharmacology, 1983, 22, 993-1000.
    • (1983) Neuropharmacology , vol.22 , pp. 993-1000
    • Colpaert, F.C.1    Janssen, P.A.2
  • 14
    • 0020615347 scopus 로고
    • Inhibition of 5-hydroxytryptamine-mediated behaviour by the putative 5-HT2 antagonist pirenperone
    • Green, A.R.; O'Shaughnessy, K.; Hammond, M.; Schachter, M.; Grahame-Smith, D.G. Inhibition of 5-hydroxytryptamine-mediated behaviour by the putative 5-HT2 antagonist pirenperone. Neuropharmacology, 1983, 22, 573-578.
    • (1983) Neuropharmacology , vol.22 , pp. 573-578
    • Green, A.R.1    O'Shaughnessy, K.2    Hammond, M.3    Schachter, M.4    Grahame-Smith, D.G.5
  • 15
    • 0021893296 scopus 로고
    • A behavioural and biochemical study in mice and rats of putative selective agonists and antagonists for 5-HT1 and 5-HT2 receptors
    • Goodwin, G.M; Green, A.R. A behavioural and biochemical study in mice and rats of putative selective agonists and antagonists for 5-HT1 and 5-HT2 receptors. Br. J. Pharmacol., 1985, 84, 743-753.
    • (1985) Br. J. Pharmacol. , vol.84 , pp. 743-753
    • Goodwin, G.M.1    Green, A.R.2
  • 16
    • 0024987703 scopus 로고
    • Withdrawal from chronic treatment with (+/-)-DOI causes super-sensitivity to 5-HT2 receptor-induced head-twitch behaviour in mice
    • Darmani, N.A.; Martin, B.R.; Glennon, R.A. Withdrawal from chronic treatment with (+/-)-DOI causes super-sensitivity to 5-HT2 receptor-induced head-twitch behaviour in mice. Eur. J. Pharmacol., 1990, 186, 115-118.
    • (1990) Eur. J. Pharmacol. , vol.186 , pp. 115-118
    • Darmani, N.A.1    Martin, B.R.2    Glennon, R.A.3
  • 18
    • 0026686986 scopus 로고
    • Behavioral evidence for differential adaptation of the serotonergic system after acute and chronic treatment with (+/- )-1-(2,5-dimethoxy-4- iodophenyl)-2-aminopropane (DOI) or ketanserin
    • Darmani, N.A.; Martin, B.R.; Glennon, R.A. Behavioral evidence for differential adaptation of the serotonergic system after acute and chronic treatment with (+/- )-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) or ketanserin. J. Pharmacol. Exp. Ther., 1992, 262, 692-698.
    • (1992) J. Pharmacol. Exp. Ther. , vol.262 , pp. 692-698
    • Darmani, N.A.1    Martin, B.R.2    Glennon, R.A.3
  • 20
    • 0021336087 scopus 로고
    • Differential actions of serotonin antagonists on two behavioral models of serotonin receptor activation in the rat
    • Lucki, I.; Nobler, M.S.; Frazer, A. Differential actions of serotonin antagonists on two behavioral models of serotonin receptor activation in the rat. J. Pharmacol. Exp. Ther., 1984, 228, 133-139. (Pubitemid 14223392)
    • (1984) Journal of Pharmacology and Experimental Therapeutics , vol.228 , Issue.1 , pp. 133-139
    • Lucki, I.1    Nobler, M.S.2    Frazer, A.3
  • 21
    • 0022569903 scopus 로고
    • 2-adrenoceptors
    • Handley, S.L.; Singh, L. The modulation of head-twitch behaviour by drugs acting on beta-adrenoceptors: evidence for the involvement of both beta 1- and beta 2-adrenoceptors. Pharmacology, 1986, 7, 320-324. (Pubitemid 16131117)
    • (1986) Psychopharmacology , vol.88 , Issue.3 , pp. 320-324
    • Handley, S.L.1    Singh, L.2
  • 24
    • 0032918170 scopus 로고    scopus 로고
    • Perspectives of non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection
    • DOI 10.1016/S0014-827X(98)00103-7, PII S0014827X98001037
    • De Clerq, E. Perspectives of non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection. Il Farmaco, 1999, 54, 26-45. (Pubitemid 29187015)
    • (1999) Farmaco , vol.54 , Issue.1-2 , pp. 26-45
    • De Clercq, E.1
  • 25
    • 69549142922 scopus 로고    scopus 로고
    • New chemistry with old ligands: N-alkyl- And N,N-dialkyl-N-acyl(aroyl) thioureas in coordination, analytical and process chemistry of the platinum group metals
    • Koch K.R. New chemistry with old ligands: N-alkyl- and N,N-dialkyl-N-acyl(aroyl)thioureas in coordination, analytical and process chemistry of the platinum group metals. Coord. Chem. Rev., 2001, 473, 216-217.
    • (2001) Coord. Chem. Rev. , vol.473 , pp. 216-217
    • Koch, K.R.1
  • 26
    • 0000531912 scopus 로고
    • Solvent Extraction of Gold with N-substituted Benzoylthiourea
    • Vest, P.; Schuster, M.; Konig, K.H. Solvent Extraction of Gold with N-substituted Benzoylthiourea. Fresenius J. Anal. Chem., 1991, 341, 566-568.
    • (1991) Fresenius J. Anal. Chem. , vol.341 , pp. 566-568
    • Vest, P.1    Schuster, M.2    Konig, K.H.3
  • 27
    • 8844266177 scopus 로고    scopus 로고
    • 6] salts, where L is ethylene- or trimethylene-thiourea, and M is Si, Ge or Sn. Five Te(II) complexes with a novel type of structure linked together by unusual N - H - F hydrogen bonds
    • 6] salts, where L is ethylene- or trimethylene-thiourea, and M is Si, Ge or Sn. Five Te(II) complexes with a novel type of structure linked together by unusual N - H - F hydrogen bonds. Polyhedron, 2004, 23, 3021-3032.
    • (2004) Polyhedron , vol.23 , pp. 3021-3032
    • Foss, O.1    Husebye, S.2    Törnroos, K.W.3    Fanwick, P.E.4
  • 28
    • 0001787386 scopus 로고
    • On the chromatography of metal chelates XIV. Thin-layer-chromatography of N,N-dialkyl-N'-benzoylthiourea-chelates
    • Konig, K.H.; Schuster, M.; Schneeweis, G.; Steinbrech, B. On the chromatography of metal chelates XIV. Thin-layer-chromatography of N,N-dialkyl-N'-benzoylthiourea-chelates. Fresenius Z. Anal. Chem., 1984, 319, 66-69.
    • (1984) Fresenius Z. Anal. Chem. , vol.319 , pp. 66-69
    • Konig, K.H.1    Schuster, M.2    Schneeweis, G.3    Steinbrech, B.4
  • 30
    • 27144549882 scopus 로고    scopus 로고
    • Synthesis, characterization and antimicrobial activities of some metal complexes with N '-(2-chloro-benzoyl)thiourea ligands: The crystal structure of fac-[CoL3] and cis-[PdL2]
    • Emen, M.F.; Arslan, H.; Kulcu, N.; Florke, U.; Duran, N. Synthesis, characterization and antimicrobial activities of some metal complexes with N '-(2-chloro-benzoyl)thiourea ligands: The crystal structure of fac-[CoL3] and cis-[PdL2]. Polish J. Chem., 2005, 79, 1615-1626.
    • (2005) Polish J. Chem. , vol.79 , pp. 1615-1626
    • Emen, M.F.1    Arslan, H.2    Kulcu, N.3    Florke, U.4    Duran, N.5
  • 31
    • 50849128166 scopus 로고    scopus 로고
    • Synthesis of 4-Amino-1,7,8,9-tetramethyl-4-aza-tricyclo [5.2.1.02,6]dec-8-ene-3,5-dione
    • Struga, M.; Kossakowski, J. Synthesis of 4-Amino-1,7,8,9-tetramethyl-4- aza-tricyclo [5.2.1.02,6]dec-8-ene-3,5-dione. Molbank, 2007, M534.
    • (2007) Molbank
    • Struga, M.1    Kossakowski, J.2
  • 32
    • 69549132896 scopus 로고    scopus 로고
    • Pharmacological studies on the central regulation of body temperature
    • Cox, B.; Lomax, P. Pharmacological studies on the central regulation of body temperature. Annu. Rev. Pharmacol. Toxicol., 1997, 17, 341-353.
    • (1997) Annu. Rev. Pharmacol. Toxicol. , vol.17 , pp. 341-353
    • Cox, B.1    Lomax, P.2
  • 33
    • 0029042334 scopus 로고
    • The protective effect of moclobemide against hypoxia-induced lethality in mice is not due to a decrease in body temperature
    • Ulugol, A.; Karadag, H.C.; Dokmeci, D.; Al.-Khatib, I.; Dokmeci, I. The protective effect of moclobemide against hypoxia-induced lethality in mice is not due to a decrease in body temperature. Pharmacol. Biochem. Behav., 1995, 51, 245-247.
    • (1995) Pharmacol. Biochem. Behav. , vol.51 , pp. 245-247
    • Ulugol, A.1    Karadag, H.C.2    Dokmeci, D.3    Al-Khatib, I.4    Dokmeci, I.5
  • 34
    • 0025810485 scopus 로고
    • Clorgyline-induced reduction in body temperature and its relationship to vigilance states in Syrian hamsters
    • Gao, B.; Jr Ducan, W.C.; Wehr, T.A. Clorgyline-induced reduction in body temperature and its relationship to vigilance states in Syrian hamsters. Neuropsychopharmacology, 1991, 4, 187-1897.
    • (1991) Neuropsychopharmacology , vol.4 , pp. 187-1897
    • Gao, B.1    Ducan Jr., W.C.2    Wehr, T.A.3
  • 35
    • 0030472746 scopus 로고    scopus 로고
    • Action of harman (1-methyl-β-carboline) on the brain: Body temperature and in vivo efflux of 5-HT from hippocampus of the rat
    • Adell A.; Bigg T.A.; Myers R.D. Action of harman (1-methyl-β- carboline) on the brain: Body temperature and in vivo efflux of 5-HT from hippocampus of the rat. Neuropharmacology, 1996, 35, 1101-1107.
    • (1996) Neuropharmacology , vol.35 , pp. 1101-1107
    • Adell, A.1    Bigg, T.A.2    Myers, R.D.3
  • 36
    • 0010520441 scopus 로고    scopus 로고
    • Oxford Diffraction. Oxford Diffraction, Wroclaw, Poland
    • Oxford Diffraction. CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Wroclaw, Poland, 2001.
    • (2001) CrysAlis CCD and CrysAlis RED
  • 37
    • 37549039510 scopus 로고    scopus 로고
    • A short history of SHELX
    • Sheldrick, G. M. A short history of SHELX. Acta Cryst., 2008, A64, 112-122.
    • (2008) Acta Cryst. , vol.A64 , pp. 112-122
    • Sheldrick, G.M.1
  • 39
    • 84951384024 scopus 로고
    • Simplified method of evaluating dose effect experiments
    • Litchfield, L.T.; Wilcoxon, F. Simplified method of evaluating dose effect experiments. J. Pharmacol. Exp. Ther., 1949, 96, 99-113.
    • (1949) J. Pharmacol. Exp. Ther. , vol.96 , pp. 99-113
    • Litchfield, L.T.1    Wilcoxon, F.2
  • 40
    • 0000680650 scopus 로고
    • Acetic acid for analgesic screening
    • Koster, R.; Anderson, M.; DeBeer, E.J. Acetic acid for analgesic screening. Fed. Proc., 1959, 18, 412-416.
    • (1959) Fed. Proc. , vol.18 , pp. 412-416
    • Koster, R.1    Anderson, M.2    Debeer, E.J.3
  • 41
    • 0344114226 scopus 로고
    • Zur pharmakologischen charakterisierung des schalafmittels doriden
    • Gross, F.; Tripod, J.; Meir, R. Zur pharmakologischen charakterisierung des schalafmittels doriden. Schweiz. Med. Wochschr., 1995, 85, 305-309.
    • (1995) Schweiz. Med. Wochschr. , vol.85 , pp. 305-309
    • Gross, F.1    Tripod, J.2    Meir, R.3
  • 42
    • 84940816667 scopus 로고
    • Une nouvelle méthode simple pour explorer l'action tranquilisante: Le test de la cheminée
    • Boissier, J.R.; Tardy, J.; Diverres, J.C. Une nouvelle méthode simple pour explorer l'action tranquilisante: le test de la cheminée. Med. Exp. (Basel.), 1960, 3, 81-84.
    • (1960) Med. Exp. (Basel.) , vol.3 , pp. 81-84
    • Boissier, J.R.1    Tardy, J.2    Diverres, J.C.3
  • 43
    • 84883846031 scopus 로고
    • A method for assessing the effects of drugs on the central actions of 5-hydroxytryptamine
    • Corne, S.J.; Pickering, R.W.; Werner, B.T. A method for assessing the effects of drugs on the central actions of 5-hydroxytryptamine. Br. J. Pharmacol., 1963, 20, 106-120.
    • (1963) Br. J. Pharmacol. , vol.20 , pp. 106-120
    • Corne, S.J.1    Pickering, R.W.2    Werner, B.T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.